Guys, personal style doesn't have to be as hard as we make it out to be. I used to be a mess at buying clothes: Something would catch my eye, I'd tried it on, and, if it fit in even a semi-flattering way and didn't make me cry when I looked at the price tag, I would buy it. This was all fine, except I was creating a closet with no internal consistency, wasting money, and then making it Goodwill's problem once a year.

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Eventually, I found a solution to the problem, and it has worked well for me: Think of yourself as a fictional character and pick out clothes for that guy. Professional Poker Player. Wall Street Analyst with Hippie Parents. Vineyard Owner. Come up with something specific and give the character a back story, so that when you see a piece of clothing and like it, you can say, "Nope, 35-Year-Old Who Skateboards to His Copywriting Job wouldn't wear that." It's easier to make decisions for fictional characters than it is for yourself. Here are three that I've used for myself over the years:

Preppy Villain. Sure, he's an asshole, but Mummy taught him the basics. He can tell good fabrics from bad, his needlepoint belt is unravelling just so, and he knows exactly when in the season to break out the white bucs. Once, when I was cast as a rich jerk in a friend's web short and I showed up to set in my own madras pants, the director said: "Oh, my God, what a perfect douche. Where did wardrobe even get those?" I said: "These clothes are actually my own." We didn't talk much for the rest of the shoot. It's a cliché, but Bradley Cooper in Wedding Crashers is the template here.

Hip Young Dean. This was the character I used in my late 20s and early 30s. He has Preppy Villain's appreciation for good craftsmanship and classic styling, but he'll throw in a modern element. A seersucker suit with a trendy sneaker. A tweed J. Press sportcoat with selvedge denim. A cashmere sweater with a Clash button on it. He'll make you pour out your open container, but he won't write you up this time. Donald Glover pulls this look off well. A classic tux with no socks? That's Hip Young Dean for you!

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Venice, CA, Restaurant Owner. This is where I am right now. He shops for fit and function—neutral colors, layers that accommodate 90-degree days and 60-degree nights, shirts that fit so well they stay tucked in even when you have to go downstairs and change a keg. Dawes frontman Taylor Goldsmith, the most understated and snappiest dresser in music today, is a good example of someone else who is channeling this character.

With that in mind, here's a roundup of some stylish guys who were out on the town last week, and my guesses at their Style Characters.

Kanye West

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Male Prostitute in 2015 Reboot of Pat Benatar's "Love Is A Battlefield" Video? Princess Leia on Ice Planet Hoth, But Male and Black and It's Summer and It's Ice Planet Hoth Fashion Week? Fashion Icon Who Has Sort of Temporarily Given Up?

Aaron Taylor-Johnson

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Rebellious Youngest Son of Texas Oil Family Who Does Acoustic Open Mics Under Assumed Names? Cattleman With Birchbox Subscription? Hozier Tour Manager?

David Letterman

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Belgian on Holiday in Monaco? Father of Criss Angel? Guy Who Is Dressing Himself for First Time Since 1982?

Joe Mangianello

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Retired NFL Guy With His Name on a Phoenix Restaurant? Crossfit Box Owner? Guy Who Can Wear Whatever the Fuck He Wants Because Look at Him?

Johnny Depp

Eddie Redmayne

Grown-up Ravenclaw, If That Shit Were Real? Trust Fund Poet? Vineyard Owner With Two Golden Retrievers?

E.J. Johnson

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Heir to Unimaginable Wealth to Whom the Concept of Feeling Inferior for Being Gay Has Literally Never Occurred, Even for One Moment? (I have no other choices for this one, because I have clearly nailed it.)